Earlier this month I was invited to Florence, Alabama, for menswear designer Billy Reid's third annual shindig, which is more or less a long, lazy weekend propped up by the three pillars of Southern hospitality: bourbon, barbecue, and badass Southern music. The latter was epitomized by a scorching, gem-like flame of an acoustic set—beneath a constellation of candle-filled Mason jars hung from Reid's storeroom ceiling—by Justin Townes Earle. An admitted dandy who's become a fit-model/muse for Reid over the last few years and was recently named one of GQ's "25 Most Stylish Men in the World," the lanky 29-year-old singer capped each tune with a thunderous stamp of his boot, which knocked several drinks off the homemade stage. In between songs, he told stories about his decade-long struggle with cocaine addiction and winked to his girlfriend, whom he lives with in Nashville and Manhattan. "People kept asking me if he was playing over recorded tracks," recalled Reid a week later. "They couldn't believe he was making all that sound out of one guitar."

Earle's latest album, Harlem River Blues, is up for two Americana Music Awards (he won Best New and Emerging Artist for his sophomore album in 2009). In it, he recounts his own tales of hard living and redemption in the city (as noted the title track), his escape from his awful first apartment ("Last Night in Brooklyn"), and various tales of his cast of new friends ("Workin' For The MTA"). In anticipation of his free concert at Brooklyn's Prospect Park Bandshell this Thursday, Earle talked about his new sound, his sartorial soul brother, the strained relationship with his father, and the "normal," if vuvuzela-backed, dream job from his childhood.

MICHAEL SLENSKE: Where you at right now?

JUSTIN TOWNES EARLE: I'm in Nashville.

SLENSKE: Are you also still living in the East Village?

EARLE: Soho, now. I moved to Brooklyn about three and a half years ago. I was living in Crown Heights when I first got up there, and it was pretty terrible, and I was living with a girl up there and getting ready to take off on a long tour, and I was going to be out of the country for a while. School had just let out for the summer in Crown Heights, and so the violence kicked off pretty quick; so two days before I left, I called a friend of mine who's a super over in the East Village of several buildings, and I got him to hook me up with an apartment and a lease and I moved into Manhattan.

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SLENSKE: You're focusing a lot on New York in Harlem River Blues. Was there one thing that pushed you in that direction?

EARLE: I moved to New York right before Midnight at the Movies came out, and New York just totally influenced my writing process at that point. And it's something I did do intentionally. I did it because Woody Guthrie did it and Lead Belly did it. There's a reason those guys came to New York, because New York has always had a love for Southern artists. There's no place else that makes me feel like the city does. I just love the immediate nature of the city, you can get whatever you want whenever you want it and do whatever you want whenever you want to.

SLENSKE: But you like ducking out to Nashville when you want, I'm sure?

EARLE: Yeah, it's nice coming to Nashville, and we have four-bedroom house and a dog, and we go swimming a lot. We get down here and spread out a lot, and I miss my sweet tea and my cornbread and my good southern cooking—but I'm down here eating pretty for two weeks and I'm ready to go back to New York City.

SLENSKE: People make a lot out of you being Steve Earle's son and named after Townes Van Zandt. Is there one you identify more with musically?

EARLE: Well, I kind of identify with them both equally. Me and my father are both very similar writers; we're both thesis writers who believe in a hard beginning, middle, end, with only the most important information being given. But my dad likes to put as many words as he can into a line, whereas I like to put as few as I can. I think a lot of men are afraid of pretty things, and I'm not, I like pretty songs, and I think that's what I take from Townes. I'm completely fearless in making pretty music. I think it's great. I don't think it takes away from my manliness at all.

SLENSKE: But by that same token, a lot of your songs are very gritty. Did you feel you had to live this hard life to write these songs?

EARLE: Well, I do think I've had to live the life I did to get these songs, but I don't think I had to live the life I did in order to write songs, period. Songwriters are just born with it. It does take practice, but I just think I'd be a different kind of songwriter.

SLENSKE: Didn't your dad say you have to live what you write?

EARLE: Well, you have to live what you write, or you have to know it. There are exceptions, like story songs, where you just have to have your facts straight. But I think you don't have to live a hard life to be a good or interesting songwriter. Weezer's a good example. They write great fucking songs. That blue record is still one of my favorite rock 'n' roll records of all time. And the songs on it are perfect, they're just written perfect for that style of music, and those boys weren't smoking crack, they were going to class.

SLENSKE: You're pretty open about your addiction onstage. Is that sort of a therapy for you or more just about being a storyteller?

EARLE: It's about being a storyteller, and it's also just a part of making my life easier because the deal is that I've been in this business for a really long time for someone my age, and I know how it works, and I understand that the stories are gonna go, they're gonna keep flying around, and if you don't say anything about it, you don't get to influence how the stories go, so I like to put my two cents in so it's not just all made up, because the stories are always way better than the truth.

SLENSKE: Any examples of that?

EARLE: There's all kinds of examples. Here's one of the reasons I have to get out of Nashville sometimes. One of my girlfriend's friends was at a bar not too long ago and somehow I became the topic of conversation, and the girl said that I was currently married, number one, and also having an affair with Jessica Lee Mayfield. And my girlfriend's friend said, "I happen to know that's not true." But the girl was insistent upon that being the truth, and that's the deal, it's just the way it works. And it's funny because me and Jessica Lee Mayfield are really, really good friends. It's just funny, people are going to tell stories, and that's not even close to the truth. I've never even been married, and that's out there. So God knows what they could do with the shit they have some minute amount of information on. My dad got mad at me because I said onstage that I was smarter than him. I said I realized when I was younger that I didn't have to marry every woman that I fucked and he got kind of upset with me about that. I do piss people with my candor sometimes, but that's just part of the game.

SLENSKE: Is there a bit of a rivalry with you and your dad in a way?

EARLE: I feel there has to be a little bit, and it's kind of weird, because for the past few years I didn't have much to talk about, but now I'm edging up on my dad, I've got his hind in sight, basically, and so when we talk nowadays pretty much all we talk is shop. "Hey, how you doing?" "Oh, I'm packing my bags to go here, I'm going to be gone for two weeks."

SLENSKE: What was it like before?

EARLE: My teens were pretty unpleasant. But it was both of our faults in a big way. I was a relentlessly unruly teenager, and I was also getting involved with some very dangerous people because of all the drugs I was getting into. I did a lot of drugs, and the only way to do a lot of drugs when you're a teenager is to sell a lot of drugs, so I was getting into a lot of trouble. I toured with my dad for two years with a full-blown fucking heroin addiction going, and that was hard for my dad, and the fact that he was about 12 years clean at the time, and I was out there going nuts. But I had every chance to not be like this. I didn't grow up around my father, I grew up around my mother, and my father was around so rarely that he couldn't even be counted as a real influence until I was in my teens. So I had every chance to just be a normal person.

SLENSKE: Meaning there was a point you thought you wouldn't be a musician?

EARLE: Yeah, my first thing that I wanted to be, what my plan was when I was five years old until I was about thirteen, was that I was going to be a professional soccer player.

SLENSKE: How did you get hooked up with Billy Reid?

EARLE: I met him through my old manager, Traci Thomas. The Americana Awards were coming up three years ago, and I wanted a ridiculous suit to wear, and she told me about Billy. When we met, we started talking about the suit, and he was getting kind of excited about the stuff I was mentioning, and he brought out a jacket and said, "What do you think of blue velvet?" I said, "That's great, but can you do it in red?" He just stopped and gasped and said, "Hell yes, we can do it in red." I think the deal with Billy is that he's supplied musicians with gear for a long time, but most of the bands like the [Drive By] Truckers, they'll just wear the shirt or the jacket or the boots—where with me, he finally found someone who will wear everything he made, right down to the bow ties and suspenders and shit.

SLENSKE: So do you consider yourself a dandy?

EARLE: Yeah, I would probably have to say that. I'm definitely a well-dressed man everywhere I go, pretty much. I feel weird if my shirt doesn't have a collar on it. Right now I'm wearing jeans and a polo shirt, but I'm wearing $250 custom-made selvage denim jeans and a Billy Reid polo. I'm way into fashion. It's definitely one of my weaknesses, and Billy and I became friends because it's really rare that you find two straight men who can sit down and have a long conversation about fabric.

SLENSKE: Do you get shit for that in the scene you're in?

EARLE: No, I don't. That's one thing my dad taught me. He said, "Wearing Marc Jacobs sweaters ain't very Americana." I said, "Well, fuck Americana, I'm not trying to be Americana." I grew up around the Grand Ole Opry and people dressed nice when they played, and I think it showed a certain amount of respect for themselves and the crowd, and so something I've done since my teens is wear a suit onstage.

SLENSKE: What's that saying, dress for your next job?

EARLE: Yeah, exactly. I say, "You rock like a god, shop like a girl."

JUSTIN TOWNES EARLE PLAYS BROOKLYN'S PROSPECT PARK BANDSHELL WITH PUNCH BROTHERS AND HACKENSAW BOYS ON THURSDAY, JUNE 30, AT 7 PM. FOR MORE ON THE ARTIST, VISIT HIS WEBSITE.